Mr.Case had vision as he recognized that the opening of the Greenwoods Turnpike, in 1799, would change the area forever. The second event to increase development occured in 1849, when the railroad came to Winsted. Furthur development was guaranteed when Wakefield Boulevard was completed in 1892. The 'Gay Nineties' made his heart pump with joy with the town water supply moving from Highland Lake to Crystal Lake on 1896. In 1897 a spur of the rail system between Winsted and Torrington, went over Case Mountain to Highland Park. The only competition was Woodland Park, opening in 1926 by Gaetano Lentini at the north end of the lake, approximately three miles away. An earlier competitor was close by at Hatch's Landing (Barton's Point). The Highland Lake Transportation Company in 1889, leased the area, built a large dining and dance hall, and a Clark Electric Generator supplied power to a large number of lights giving it the name, Electric Park. They distributed a beautiful, New York style, advertising booklet called, "A Day's Outing by Water And Rail'. Two passenger boats, steamers, Blanche and the Highland were on an hourly schedule from Steamboat Landing to this park. This transportation company stopped doing business two years later. During the decade five passenger boats were in business, Iron Clad, Tunxis, Blanche, Highland and Carrie.

At the northern end of Case Mountain, stone pillar gates, were erected at the eastern end of Rockwell Street. Dirt roads were put in place for a short distance. For years these roadways were the pathway for the neighborhood kids on their way past the Mead House, up and over the ridge to 'Robbers Cave'. This area never became developed although early maps are marked, Highland Park. The last big event to the 'Gay Nineties', for this area, was the opening of Lookout Pleasure Park, at the top of Pratt Street. The name was soon shortened to Lookout Park.

Prior to the "Roaring Twenties" the property, on the lake was owned by The Connecticut Company with electric power supplied by the trolley line. Many New Yorkers who frequented this area referred to it as "Little Coney Island" or Electric Park. Allow yourself to dream, visualize getting on the trolley car near the Hotel Winchester. The open car proceeds down Main, over Rowley toward Torrington. Changing cars they proceed up the road, through the cool woods until a clearing becomes visible. The area was approximately 500 square feet on the east side of Wakefield Boulevard. On the right rear was the men's toilet while near the road was a restaurant. On the left rear was a large dining room, behind a small cottage. Closer to the road, was the nursery building while near the tracks was the meter house. On the far left center of this parcel was the ladies toilet. Getting off the trolley near the road you had a good, downhill view, of the lake and other buildings. This section of the park was approximately 200 feet deep, and 500 feet long at the shore line. Directly across the road from the trolley stop was a pop corn stand. Back right was a large dance pavilion, near the water a large float for the steamers and a boat house. The buildings by the water, looking south towards Bristols Cove, from the pavilion were a blanket stand, ice cream parlor, doll stand, candy stand, and bath house. On the left, closer to the road was a shooting gallery, and a merry-go-round.

Later a wooden slide into the lake was built and became popular. One person at a time sitting on a wooden cart went down the slide into the water. I for one found joy from the experience. The sun is shining, the Blanche is at the float, it is time for a boat ride.

The steamer with a curtain top, gave all a smooth ride on the sparkling water. Looking out the right side we soon were passing Point Comfort, Loon Island, Perch Rock, Indian Point, and then for a short stop at Steamboat Landing. After stretching the legs we proceed on the tour up the other side of the lake passing The Tablet, Cold Springs, Trout Rock, Turtle Island, Wintergreen Island, Small Island, Large Island, Crystal Spring, and back to Highland Park. It was expensive, twenty five cents, but I want to do it again with someone special.

The park was run by Samual Bennet and D.V O'Connel during this period. Name bands from around the country played at the dance pavilion with large crowds in attendance. In 1921 a permit from the State Police to conduct Sunday dances at the pavilion was obtained. Local residents gave severe resistance to this plan with the result being that the oeners stopped having the Sunday dances. At one time, the dates I can not confirm, an outdoor theater was in operation at this site. From the picture I have, I would estimate the period was the twenties.